Benzyl Bromide → HCID 22629692, compound

HRID 277054Notes

Reaction equation

HRID 277054 reaction equation
[C:1]1([C:7]2[N:22]=[C:10]3[CH:11]=[C:12]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[CH:13]=[C:14]([NH2:15])[N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)(O)[O-].[Na+]>CS(C)=O>[CH2:25]([N:15]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:14]1[N:9]2[N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:22]=[C:10]2[CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:13]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 226297002-Phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Product 1

HCID 22629692HCID 22629692, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.20 g (0.0007 mol) 2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine in 17.5 ml dimethylsulfoxide was treated with 0.69 g (0.01 mol) potassiumhydroxide(85%) for 20 minutes at room temperature. Then 0.26 g (0.0015 mol) benzylbromide were added and stirring was continued for 70 hours. Saturated aqueous sodiumbicarbonate was added and the mixture was extracted with chloroform. Evaporation of the solvent and chromatography on silicagel with dichloromethane/methanol 98/2 and crystallisation from diethylether gave 0.12 g (44%) dibenzyl-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-amine as light brown crystals. MS m/e (%): 468 (M+H+, 100).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. customEvaporation of the solvent and chromatography on silicagel
  3. customwith dichloromethane/methanol 98/2 and crystallisation from diethylether

Sources & evidence

ORD record
ord-d0eb86f7c4604ec39d5852d9c26501f1
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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